My view however is that this isn't wealthy. Instead this is where the middleclass should be. I don't make enough to retire early (though i could probably extreme FIRE, but that doesn't sound enjoyable to me). I'm not by my definition wealthy, just safe, satisfied, happy. No fancy cars or homes, just a stable honest and predictable living. These are traits that, in my mind, America should strive to bring to all people.
Unfortunately i've not seen this spread. I've only seen it decrease. People far more and more on the edge of collapse, with no safety net in their bank, no budget for emergency expenses, no possibility of retirement.
Relative to the current state of America i am wealthy. To me that is very, very sad.
Job loss is the only big worry, and even in that situation it wouldn't be difficult to find a similar job with similar pay. I know that is a comfort that not everyone(or most people) has. Knowing that this seems to be "as good as it gets" when compared to the majority of Americans is what makes me very, very sad.
Point being, I think people are more aware of the unattained wealth above them than the levels they've already surpassed. (Myself included). The comment you replied to strikes me in the same way, though not nearly as blatant!
Fast forward... I own a house in a rural area and have a family. I'll likely never have that cabin in the mountains, and I'll never be free of having to support my family. That's my fault though..I took the path of least resistance and ended up where I'm at - I didn't take the path towards what I dreamed about having as a kid.
Regardless, perhaps make it a goal to do this when you retire. It will give you something to work toward and possibly quell some of your regret.
If it's on your mind this much, and I'm no expert here, you might want to talk about it with a professional. You can't let this stuff bottle up and eat away at you from the inside.